Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B41/00—Special methods of performing the coupling reaction
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B41/00—Special methods of performing the coupling reaction
  • C09B41/001—Special methods of performing the coupling reaction characterised by the coupling medium
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0001—Post-treatment of organic pigments or dyes
  • C09B67/002—Influencing the physical properties by treatment with an amine
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/006—Preparation of organic pigments
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/006—Preparation of organic pigments
  • C09B67/0065—Preparation of organic pigments of organic pigments with only non-macromolecular compounds
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D11/00—Inks
  • C09D11/02—Printing inks
  • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
  • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment

Definitions

• Azo pigments particularly useful in printing inks e.g. in illustration gravure, find application.
• This compound is commercially available and is usually present as a mixture of three stereoisomers, the cis.cis isomer, the cis, trans isomer and the trans.trans isomer, it being found that the trans, trans content is below 20% :
• 4,4'-diamino-dicyclohexyl-methane with high trans, trans content is of importance for the large-scale production of polyurethane elastomers with improved material properties, such as temperature stability and solvent resistance (DE 43 34 790 A1).
• the present invention therefore provides an azo pigment preparation characterized by a content of 4,4'-diamino-dicyclohexylmethane, the proportion of the trans, trans isomer being at least 25%, based on the total amount of 4,4'-diamino dicyclohexylmethane.
• trans.trans isomer The preparation of pure trans.trans isomer is technically complicated. Although the use of pure trans, trans isomer is possible, it is not necessary for the purposes of the present invention. For economic and technical reasons, it is sufficient to limit the proportion of the trans, trans isomer to 25 to 75%, in particular 35 to 60%, based on the total amount of 4,4'-diamino-dicyclohexylmethane. It was found that regardless of the total amount of 4,4'-diamino-dicyclohexyl-methane used, the proportion of the ice, ice and ice, trans isomers in the total isomer mixture should not be higher than 75%. Perturbation of the crystal lattice of the azo pigment by non-planar stereoisomers may be responsible for degrading coloristic properties.
• a stereoisomer mixture having an inventive trans, trans content is expediently from 2 to 30% by weight, preferably from 5 to 20% by weight, based on the weight of the azo pigment.
• Suitable azo pigments are all products used in printing inks, preferably diaryl yellow pigments, in particular the acetoacetylarylamide series. Particularly preferred are Cl. Pigment Yellow 12, 13, 14, 17, 55, 63, 81, 83, 87, 90, 106, 113, 114, 121, 124, 126, 127, 136, 152, 170, 171, 172, 174, 176 and 188, as well as Cl. Pigment Red 53: 1. Most preferably, Cl is. Pigment Yellow 12.
• the azo pigment preparations according to the invention preferably also contain long-chain aliphatic primary amines having 6 to 30 carbon atoms, such as, for example, coconut fatty amine, oleylamine, stearylamine, tallow fatty amine, alkylalkylenediamines, such as e.g. Tallow fat propylene diamine, or tallow fat dipropylene triamine.
• the content of the long-chain aliphatic primary amines having 6 to 30 carbon atoms is preferably 1 to 30 wt .-%, in particular 5 to 20 wt .-%, based on the total weight of the azo pigment preparation.
• their salts e.g. Acetates are used.
• the quantitative ratio of the long-chain aliphatic primary amine to 4,4'-diamino-dicyclohexyl-methane can vary within certain limits and depends on the desired properties of the respective pigment. The best relations are easily determined by simple preliminary tests. It may furthermore be advantageous to use from 1 to 25% by weight, in particular from 2 to 20% by weight, based on the total weight of the azo pigment preparation, of an additive from the group of fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, quaternary ammonium salts of fatty amines and fatty amine N; oxides or a combination thereof.
• Examples are stearyltrimethylammonium chloride, cetyltrimethylammonium chloride, cocoalkyltrimethylammonium chloride, cocoalkyldimethylbenzylammonium chloride, dodecylbenzyldimethylammonium chloride, dicocoalkyldimethylammonium chloride, distearyldimethylammonium chloride, ditallow fatty alkyl dimethyl ammonium chloride and cocoalkyl dimethyl amine oxide.
• the pigment preparations according to the invention may contain, in addition to the components mentioned, further customary auxiliaries or additives, such as, for example, surfactants, nonpigmentary and pigmentary dispersants, fillers, setting agents, resins, waxes, defoamers, antidusting agents, extenders, antistatic agents, colorants for shading, preservatives, drying retardants, additives for the control of rheology, wetting agents, antioxidants, UV absorbers and light stabilizers, biocides, or a combination thereof, preferably in an amount of 0.1 to 25 wt .-%, in particular 0.5 to 15 wt .-%, based on the total weight of the pigment preparation.
• auxiliaries or additives such as, for example, surfactants, nonpigmentary and pigmentary dispersants, fillers, setting agents, resins, waxes, defoamers, antidusting agents, extenders, antistatic agents, colorants for shading, preservatives, drying retardants, additives for the control of
• the invention also provides a process for the preparation of an azo pigment preparation, characterized in that the 4,4'-diamino-dicyclohexyl-methane with a trans, trans content of at least 25% before, during or after the azo coupling, but before the Isolation of the azo pigment is added.
• the 4,4'-diamino-dicyclohexyl-methane with a trans, trans content of at least 25% before, during or after the azo coupling, but before the Isolation of the azo pigment is added is used as a precipitation aid in the precipitation of the coupling component, added after the coupling of the dome stock or only the press cake prepared with it.
• it can be added in a subsequent finishing process.
• the further work-up of the pigment suspension is carried out by customary methods, such as filtration, washing, drying and milling.
• a readily dispersible azo pigment preparation is obtained, which gives very strong, readily flowable printing ink, in particular toluene-based gravure printing inks, with which glossy and non-penetrating prints are obtained.
• the pigment preparations according to the invention can be used for pigmenting high molecular weight organic materials of natural or synthetic origin, for example plastics, resins, paints, paints, electrophotographic toners and developers, electret materials, color filters and inks, printing inks and seeds. However, their use is particularly preferred for the production of printing inks, in particular gravure inks based on toluene.
• the invention also provides a printing ink, in particular gravure ink, which contains the azo pigment preparation according to the invention.
• DCB 3,3'-dichlorobenzidine
• the coupling reaction is carried out by metering the DCB tetrazole solution into the precipitated coupling component at below the surface at a continuous rate over a period of 60 minutes. After the reaction has ended, the temperature is raised to 40 ° C. and 2.5 g of dodecylbenzyldimethylammonium chloride, 10 g of tallow fatty alkylpropylenediamine and 4.8 g
• the pigment preparation prepared according to Example 1 has good dispersibility and is characterized in that it can be made from toluene-based gravure inks which give very glossy and non-penetrating prints with high optical density.
• An azo pigment preparation is prepared in accordance with Example 1, with the difference that 4,4'-diamino-dicyclohexylmethane having a trans.trans content of 25% is used.
• a prepared according to Example 2 pigment preparation provides compared to Example 1, a gravure ink with slightly increased viscosity and prints with good gloss and comparable optical densities.
• An azo pigment preparation according to Example 1 is prepared, with the difference that 4,4'-diamino-dicyclohexylmethane having a trans.trans content of about 20% is used.
• a pigment preparation prepared in accordance with the comparative example gives a gravure ink of markedly increased viscosity and prints produced therefrom with lower gloss, lower color strength and significantly lower optical densities.
• An azo pigment preparation according to Example 1 is prepared, with the difference that 7.4 g of 4,4'-diamino-dicyclohexyl-ethane are used.
• a prepared according to Example 3 pigment preparation provides in comparison to Example 1, a gravure ink with redder hue, prints produced therefrom are characterized by improved gloss and higher optical densities, especially at large pelvic depths.
• Example 4 An azo pigment preparation according to Example 1 is prepared, with the difference that the 4,4'-diamino-dicyclohexylmethane is added before the coupling step. This gives a product with comparable properties.
• An azo pigment preparation according to Example 1 is prepared, with the difference that the 4,4'-diamino-dicyclohexyl-methane is added after filtration to the press cake.
• the press cake is then homogenized, dried and ground. This gives a product with comparable properties.
• An azo pigment preparation according to Example 1 is prepared, with the difference that 6 g of the acetoacetanilide used are replaced by 7 g of acetoacetic p-anisidide. This gives a reddish product.
• An azo pigment preparation according to Example 1 is prepared, with the difference that 2.8 g of the acetoacetanilide are replaced by 4.7 g of the potassium salt of p-acetoacetylaminobenzenesulfonic acid. This gives a pigment preparation, which gives a greenish gravure ink compared to Example 1, prints produced therefrom are characterized by increased transparency.
• Example e P.Y.
• An azopigment preparation according to Example 1 is prepared, with the difference that 6 g of the acetoacetanilide used are replaced by 6.5 g of acetoacetic p-toluidide.
• a reddish product is obtained, and a toluene-based gravure ink prepared therefrom provides prints with improved optical density.
• Example 1 An azo pigment preparation according to Example 1 is prepared, with the difference that the tallow fat propylene diamine used is replaced by tallow fat dipropylene triamine. This gives a greenish pigment preparation with comparable good properties to those of Example 1.
• An azo pigment preparation according to Example 9 is prepared, with the difference that the tallow fat dipropylene triamine is added before the coupling step. This gives a pigment preparation with comparable good properties.
• Example 11 Mixture of P.O. 13 + P.Y.12
• the coupling reaction is carried out by adding as much to a DCB tetrazo solution prepared according to Example 1 until a slight excess of diazo can be detected.
• the precipitated acetoacetanilide is added to the reaction mixture and the coupling reaction is completed with the aid of the remaining DCB tetrazo solution.
• the further preparation of the pigment is carried out according to the procedure of Example 1. Compared to Example 1 to obtain a rotstichigere pigment preparation, a printing ink prepared from this is lower viscosity and color strength in the print.

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• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Organic Chemistry (AREA)
• General Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Wood Science & Technology (AREA)
• Inks, Pencil-Leads, Or Crayons (AREA)

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• 2005
  • 2005-12-21 DE DE102005061066A patent/DE102005061066A1/de not_active Withdrawn
• 2006
  • 2006-11-16 WO PCT/EP2006/010980 patent/WO2007079813A1/de active Application Filing
  • 2006-11-16 KR KR1020087014797A patent/KR20080078676A/ko not_active Application Discontinuation
  • 2006-11-16 JP JP2008546157A patent/JP5317700B2/ja not_active Expired - Fee Related
  • 2006-11-16 DK DK06818571T patent/DK1966323T3/da active
  • 2006-11-16 CN CN2006800383619A patent/CN101287802B/zh not_active Expired - Fee Related
  • 2006-11-16 DE DE502006004558T patent/DE502006004558D1/de active Active
  • 2006-11-16 EP EP06818571A patent/EP1966323B1/de not_active Not-in-force
  • 2006-11-16 ES ES06818571T patent/ES2329617T3/es active Active
  • 2006-11-16 CA CA002627767A patent/CA2627767A1/en not_active Abandoned
  • 2006-11-16 US US12/086,930 patent/US7645336B2/en not_active Expired - Fee Related

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